European Journal of Chemistry 2015, 6(1), 63-70. doi:10.5155/eurjchem.6.1.63-70.1147

Synthesis of some new fluorine substituted thiobarbituric acid derivatives as anti HIV1 and cyclin-dependent kinase 2 (CDK2) for cell tumor division: Part I


Abdulrahman Salim Al-Harbi (1,*) , Reda Mohammady Abdel-Rahman (2) , Abdullah Mohamed Asiri (3)

(1) Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, 21589, Kingdom of Saudi Arabia
(2) Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, 21589, Kingdom of Saudi Arabia
(3) Centre of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia
(*) Corresponding Author

Received: 11 Sep 2014, Accepted: 18 Oct 2014, Published: 31 Mar 2015

Abstract


New potential enzyme inhibitors, fluorine-substituted thiobarbituric acid derivatives (2, 3, 9, 8 and 12) and their fused/isolated heterocyclic nitrogen systems (5, 6, 10 and 14) have been obtained from heterocyclization of fluorinated N, Nʹ-disubstituted thiourea (1, 7 and 11) with malonic acid followed by ring closure reactions with primary nitrogen reagents. Structures of the synthesized products have been deduced from their elemental analysis and spectral data. Anti-HIV-1 and inhibition of cyclin-dependent kinase2 (CDK2) for cell tumor division for the synthesized compounds were also evaluated.


Keywords


CDK2; Anti HIV; Synthesis; Heterocyclic; Potential inhibitors; Fluorinated thiobarbituric

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DOI: 10.5155/eurjchem.6.1.63-70.1147

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[1]. Reda M. Abdel-Rahman, Rihab F. Angawi, Aisha R. Al-Mehmadi
Synthesis and biological evaluation of fluorine substituted pyrazolo[4,3-e][1,2,4]triazines as purine analogues
Journal of Saudi Chemical Society  21(4), 495, 2017
DOI: 10.1016/j.jscs.2016.11.004
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[2]. Mohammed Saleh Tawfek Makki, Reda Mohammady Abdel Rahman, Ola Ahmad Abu Ali
Synthesis of New Fluorinated 1,2,4-Triazino [3,4-b][1,3,4]thiadiazolones as Antiviral Probes-Part II-Reactivities of Fluorinated 3-Aminophenyl-1,2,4-triazinothiadiazolone
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DOI: 10.4236/ijoc.2015.53017
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[3]. Zhengyi Li, Yuan Chen, Yue Yin, Zhiming Wang, Xiaoqiang Sun
Convenient Synthesis of Unsymmetrical N,N′-disubstituted Thioureas in Water
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DOI: 10.3184/174751916X14760947474916
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[4]. Srinivasa Rao Ramisetti, Manoj K. Pandey, Sang Y. Lee, Deepkamal Karelia, Satya Narayan, Shantu Amin, Arun K. Sharma
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DOI: 10.1016/j.ejmech.2017.11.006
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References

[1]. Abdel-Rahman, R. M. Pharmazie 2001, 56, 18-22.

[2]. DeClercq, E. Biochi. Biophys. Acta 2002, 1587, 258-275.
http://dx.doi.org/10.1016/S0925-4439(02)00089-3

[3]. Gulnik, S. V.; Elena, A.; Micheal, E. HIV-1 Protease Inhibitors as Antiretroviral Agents. Enzyme Inhibition in Drug Discovery and Development: The Good and the Bad. Chuang Lu and Albert P. Li, Wiley, OU 143 E605. 2009.

[4]. Sabir, S. M.; Salman, S. M.; Rbcha, J. B. T. Toxicol. Appl. Pharm. 2012, 34, 446-453.

[5]. Fernandez, J.; Perez-Alvarez, J. A.; Fernandez-Lopez, A. Food Chem. 1997, 59(3), 345-353.
http://dx.doi.org/10.1016/S0308-8146(96)00114-8

[6]. Castrejon, S. E.; Yatsimirsky, A. K. Talanta 1977, 44, 951-957.
http://dx.doi.org/10.1016/S0039-9140(96)02141-8

[7]. Vyncke, W. Fett. Wiss. Technol. 1970, 72, 1084-1087.

[8]. Lee, J. H.; Lee, S.; Park, M. Y.; Man, H. Virol. J. 2011, 8, 18-21.
http://dx.doi.org/10.1186/1743-422X-8-18

[9]. Ma, L.; Li, S.; Zheng, H.; Chen, J.; Lin, L.; Ye, X.; Chen, Z.; Xu, Q.; Chen, T.; Yang, J.; Qiu, N.; Wang, G.; Peng, A.; Ding, Y.; Wei, Y.; Chen, L. Eur. J. Med. Chem. 2011, 46, 2003-2010.
http://dx.doi.org/10.1016/j.ejmech.2011.02.033

[10]. Srivastava, A. V. K.; Kumar, A. Bioorg. Med. Chem. 2004, 12, 1257-1264.
http://dx.doi.org/10.1016/j.bmc.2003.08.035

[11]. Pothiwong, W.; Laorpaksa, A.; Pirarat, N.; Sirisawadi, S.; Intarapaya, J.; Jianmongkol, S. J. Pharmacol. Toxicol. 2007, 56, 336-338.
http://dx.doi.org/10.1016/j.vascn.2007.08.004

[12]. Zhang, D.; Zhang, J.; Li, M.; Li, W.; Aimaite, G.; Tuersun, G.; Ye, J. Food. Chem. 2011, 129, 206-212.
http://dx.doi.org/10.1016/j.foodchem.2011.04.025

[13]. Rajamaki, S.; Innitzer, A.; Falciani, C.; Tantori, C.; Christ, F.; Witvrouw, M.; Debyser, Z.; Massa, S.; Botta, M. Bioorg. Med. Chem. Lett. 2009, 19, 3615-3618.
http://dx.doi.org/10.1016/j.bmcl.2009.04.132

[14]. Haddad, E.; Jambazian, P.; Karunia, M.; Tanzman, J.; Sabate, J. Nutr. Res. 2006, 26, 397-402.
http://dx.doi.org/10.1016/j.nutres.2006.06.022

[15]. Lapenna, D.; Ciofani, G.; Pierdonenico, S. D.; Giamberardino, M. A.; Cuccurullo, F. Free Radical Bio. Med. 2001, 31(3), 331-335.
http://dx.doi.org/10.1016/S0891-5849(01)00584-6

[16]. Samir, B.; Abd El-Gaber, T.; Ahmed, A. F. Phosphorus Sulfur 2007, 182, 1915-1936.
http://dx.doi.org/10.1080/10426500701415907

[17]. Makki, M. S. T.; Abdel-Rahman, R. M. Int. J. Chem. 2011, 3, 181-192.
http://dx.doi.org/10.5539/ijc.v3n1p181

[18]. Smart, B. E. J. Fluorine Chem. 2001, 109, 3-11.
http://dx.doi.org/10.1016/S0022-1139(01)00375-X

[19]. Yonrtoku, Y.; Kubota, H.; Okamoto, Y.; Toyoshima, A.; Funtsu, M.; Ishikawa, J.; Takeuchi, M.; Ohta, M.; Tsukamoto, S. Bioorgan. Med Chem. 2006, 14, 4750-4760.

[20]. Dlavi, V. H.; Rossky, P. J. P. Natl. Acad. Sci. USA 2010, 107, 13603-13607.
http://dx.doi.org/10.1073/pnas.0915169107

[21]. Brassard, J. D.; Sakar, D.; Perron, J. Appl. Sci. 2012, 2, 453-464.
http://dx.doi.org/10.3390/app2020453

[22]. Mutlib, A.; Shockcor, J.; Chen, S. Y.; Espina, R.; Lin, J.; Graciani, N.; Prakash, S.; Gan, L. S. Drug Metab. Dispos. 2001, 29, 1296-1306.

[23]. Abdel-Rahman, R. M.; Makki, M. S. T.; Ali, T. E.; Ibrahim, M. A. Curr. Org. Synth. 2009, 10, 136-160.

[24]. Al-Harbi, A. S.; Abdel-Rahman, R. M.; Asiri A. M. Int. J. Org. Chem. 2014, 4, 142-153.
http://dx.doi.org/10.4236/ijoc.2014.42016

[25]. Abdel-Rahman, R. M.; Makki, M. S. T.; Bawazir, W. A. E-J. Chem. 2010, 7(S1), S93-S102.

[26]. Abdel-Rahman, R. M.; Makki, M. S. T.; Bawazir, W. A. E-J. Chem. 2011, 8(1), 405-414.

[27]. Makki, M. S. T.; Bakhotmah, D. A.; Abdel-Rahman, R. M. Int. J. Org. Chem. 2012, 2, 49-55.
http://dx.doi.org/10.4236/ijoc.2012.21009

[28]. Fikry, R. M. Indian J. Heterocy. Ch. 1995, 4, 265-268.

[29]. Makki, M. S. T.; Abdel-Rahman, R. M.; El-Shahawy, M. S. Int. J. Chem. 2011, 3(1), 181-192.
http://dx.doi.org/10.5539/ijc.v3n1p181

[30]. Makki, M. S. T.; Bakhotmah, D. A.; Abdel-Rahman, R. M.; El-Shahawy, M. S. Int. J. Org. Chem. 2012, 2, 311-320.
http://dx.doi.org/10.4236/ijoc.2012.223043

[31]. Makki, M. S. T.; Abdel-Rahman; R. M.; El-Shahawi, M. S. C. R. Chem. 2012, 15, 617-626.
http://dx.doi.org/10.1016/j.crci.2012.05.004

[32]. Abdel-Rahman, R. M.; El-Mahdy, K. Heterocycles 2012, 85(10), 2391-2414.
http://dx.doi.org/10.3987/REV-12-745

[33]. Ali, T. E.; Abdel-Rahman, R. M.; Hanafy, F. I.; El-Edfawy, S. M. Phosphorus Sulfur 2008, 183, 2565-2577.
http://dx.doi.org/10.1080/10426500801967864

[34]. Ibrahim, M. A.; Abdel-Rahman, R. M; Abdel-Halim, A. M.; Ibrahim, S. S.; Allimony, H. A. J. Braz. Chem. Soc. 2009, 20(7), 1275-1286.
http://dx.doi.org/10.1590/S0103-50532009000700012

[35]. Rael, L. T.; Thomas, G. W.; Craun, M. L.; Curtis, C. G.; Bar-Or, R.; Bar-Or, D. J. Biochem. Mol. Biol. 2004, 37(6), 749-752.
http://dx.doi.org/10.5483/BMBRep.2004.37.6.749

[36]. Tomei, L.; Altamura, S.; Bartholomew, L.; Bioccio, A.; Ceccacci, A.; Pacini, L.; Narjes, F.; Gennari, N.; Bisbocci, M.; Incitti, I.; Orsatti, L.; Harper, S.; Stansfield, I.; Rowley, M.; De Francesco, R.; Migliaccio, G. J. Virol. 2003, 77, 13225-13231.
http://dx.doi.org/10.1128/JVI.77.24.13225-13231.2003

[37]. Seefl, L. B.; Hoofnagle, J. H. Clin. Liver Dis. 2003, 7(1), 261-287.
http://dx.doi.org/10.1016/S1089-3261(02)00078-8

[38]. Lee, S.; Lee, G.; Kee, Y.; Park, M.; Myung, H. Virus Res. 2005, 114, 158-163.
http://dx.doi.org/10.1016/j.virusres.2005.06.010

[39]. Beaulieu, P. L. Curr. Opin. Invest. Dr. 2007, 8(8), 614-634.

[40]. Weislow, O. W.; Kiser, R.; Fine, D. L.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer. I 1989, 81(8), 577-586.
http://dx.doi.org/10.1093/jnci/81.8.577

[41]. Balas, V. I.; Verginadis, I. I.; Geromichalos, G. D.; Kourkoumelis, N.; Male, L.; Hursthouse, M. B.; Repana, K. H.; Yiannaki, E.; Charalabopoulos, K.; Bakas, T.; Hadjikakou, S. K. Eur. J. Med. Chem. 2001, 46, 2835-2844.
http://dx.doi.org/10.1016/j.ejmech.2011.04.005

[42]. Krystof, V.; Cankar, P.; Frysova, I.; Slouka, J.; Kontopidis, G.; Dzubak, P.; Hajduch, M.; Srovnal, J.; DeAzevedoJr, W. F.; Orsag, M.; Paprskarova, M.; Rolcik, J.; Latr, A.; Fischer, P. M.; Strnad., M. J. Med. Chem. 2006, 49, 6500-6509.

[43]. Matthews, D. J.; Gerritsen, M. E. Targeting Protein Kinases for Cancer Therapy. John Wiley & Sons Inc. Hoboken: New Jersey, 2010.
http://dx.doi.org/10.1002/9780470555293


How to cite


Al-Harbi, A.; Abdel-Rahman, R.; Asiri, A. Eur. J. Chem. 2015, 6(1), 63-70. doi:10.5155/eurjchem.6.1.63-70.1147
Al-Harbi, A.; Abdel-Rahman, R.; Asiri, A. Synthesis of some new fluorine substituted thiobarbituric acid derivatives as anti HIV1 and cyclin-dependent kinase 2 (CDK2) for cell tumor division: Part I. Eur. J. Chem. 2015, 6(1), 63-70. doi:10.5155/eurjchem.6.1.63-70.1147
Al-Harbi, A., Abdel-Rahman, R., & Asiri, A. (2015). Synthesis of some new fluorine substituted thiobarbituric acid derivatives as anti HIV1 and cyclin-dependent kinase 2 (CDK2) for cell tumor division: Part I. European Journal of Chemistry, 6(1), 63-70. doi:10.5155/eurjchem.6.1.63-70.1147
Al-Harbi, Abdulrahman, Reda Mohammady Abdel-Rahman, & Abdullah Mohamed Asiri. "Synthesis of some new fluorine substituted thiobarbituric acid derivatives as anti HIV1 and cyclin-dependent kinase 2 (CDK2) for cell tumor division: Part I." European Journal of Chemistry [Online], 6.1 (2015): 63-70. Web. 22 Oct. 2019
Al-Harbi, Abdulrahman, Abdel-Rahman, Reda, AND Asiri, Abdullah. "Synthesis of some new fluorine substituted thiobarbituric acid derivatives as anti HIV1 and cyclin-dependent kinase 2 (CDK2) for cell tumor division: Part I" European Journal of Chemistry [Online], Volume 6 Number 1 (31 March 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.1.63-70.1147

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